KR102622644B1 - 해충 방제제로서의 헤테로시클릭 화합물의 유도체 - Google Patents

Info

Publication number

KR102622644B1

KR102622644B1 KR1020207012183A KR20207012183A KR102622644B1 KR 102622644 B1 KR102622644 B1 KR 102622644B1 KR 1020207012183 A KR1020207012183 A KR 1020207012183A KR 20207012183 A KR20207012183 A KR 20207012183A KR 102622644 B1 KR102622644 B1 KR 102622644B1

Authority

KR

South Korea

Prior art keywords

cycloalkyl

alkyl

species

formula

cyclopropyl

Prior art date

2017-10-04

Links

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• 241000607479 Yersinia pestis Species 0.000 title claims abstract description 37
• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 315
• 238000000034 method Methods 0.000 claims abstract description 68
• 238000002360 preparation method Methods 0.000 claims abstract description 60
• 241001465754 Metazoa Species 0.000 claims abstract description 49
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 280
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 188
• -1 cyanocyclopropyl Chemical group 0.000 claims description 170
• 239000001257 hydrogen Substances 0.000 claims description 161
• 229910052739 hydrogen Inorganic materials 0.000 claims description 161
• 229910052757 nitrogen Inorganic materials 0.000 claims description 94
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 92
• 150000002431 hydrogen Chemical class 0.000 claims description 69
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 53
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 50
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 35
• 150000002367 halogens Chemical class 0.000 claims description 35
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 33
• 239000000575 pesticide Substances 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 18
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 18
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 239000004606 Fillers/Extenders Substances 0.000 claims description 8
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 8
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 7
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 6
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000004094 surface-active agent Substances 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 3
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
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• 241000894007 species Species 0.000 description 54
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• 239000000203 mixture Substances 0.000 description 50
• 125000001424 substituent group Chemical group 0.000 description 50
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• 125000000623 heterocyclic group Chemical group 0.000 description 45
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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• 239000002585 base Substances 0.000 description 38
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 34
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 description 31
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 31
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 30
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 29
• 230000002829 reductive effect Effects 0.000 description 29
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• 239000003795 chemical substances by application Substances 0.000 description 26
• 239000003112 inhibitor Substances 0.000 description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 26
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 26
• 238000011282 treatment Methods 0.000 description 26
• 125000003118 aryl group Chemical group 0.000 description 25
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 150000003254 radicals Chemical class 0.000 description 24
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 22
• 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 description 22
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 22
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 20
• 125000004093 cyano group Chemical group *C#N 0.000 description 20
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• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 18
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
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• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 14
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